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Phthaloyl chloride

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Identification
Molecular formula
C8H4Cl2O2
CAS number
88-95-9
IUPAC name
benzene-1,2-dicarbonyl chloride
State
State

Phthaloyl chloride is typically found in a liquid state at room temperature. It can be irritating to the eyes, respiratory system, and skin, and should be handled with care.

Melting point (Celsius)
-1.00
Melting point (Kelvin)
272.00
Boiling point (Celsius)
275.00
Boiling point (Kelvin)
548.00
General information
Molecular weight
203.01g/mol
Molar mass
203.0130g/mol
Density
1.4195g/cm3
Appearence

Phthaloyl chloride is a colorless to pale yellow liquid that may have a sharp and pungent odor. The liquid is clear and tends to fume when exposed to air due to hydrolysis, releasing hydrogen chloride gas.

Comment on solubility

Solubility of Benzene-1,2-Dicarbonyl Chloride

Benzene-1,2-dicarbonyl chloride, with the chemical formula C8H6Cl2O2, exhibits interesting solubility characteristics that can influence its applications in various chemical processes.

When assessing the solubility of this compound, several key points should be considered:

  • Polarity: Benzene-1,2-dicarbonyl chloride features both carbonyl and chloride functional groups, which can contribute to its overall polarity.
  • Solvent Compatibility: This compound is generally soluble in organic solvents such as chloroform, ethyl acetate, and acetone due to the nonpolar aromatic benzene ring balanced with the polar functional groups.
  • Water Solubility: However, it shows limited solubility in water, primarily due to its hydrophobic benzene rings that resist interaction with water molecules.
  • Temperature Dependency: The solubility of benzene-1,2-dicarbonyl chloride can also vary with temperature, generally being higher at elevated temperatures.

In summary, the solubility of benzene-1,2-dicarbonyl chloride is characterized by its preferential solubility in organic solvents while remaining largely insoluble in water. This behavior highlights the importance of selecting the appropriate solvent for its use in various chemical reactions and applications. As stated in literature, "the choice of solvent can significantly impact the outcome of a chemical process,” emphasizing the need for careful consideration in laboratory settings.

Interesting facts

Interesting Facts about Benzene-1,2-dicarbonyl Chloride

Benzene-1,2-dicarbonyl chloride, also known as o-phthaloyl chloride, is an intriguing organic compound that plays a significant role in various chemical reactions and syntheses. Here are some interesting facts that highlight its importance and unique characteristics:

  • Versatile Building Block: Due to its functional groups, benzene-1,2-dicarbonyl chloride serves as an essential building block in organic synthesis, particularly in the manufacture of dyes, pharmaceuticals, and agrochemicals.
  • Reactivity: The presence of two acyl chloride groups in the compound greatly enhances its reactivity, allowing for the easy formation of esters and amides with various nucleophiles.
  • Condensation Reactions: It is commonly used in condensation reactions, making it a valuable reagent for synthesizing complex structures in organic chemistry. The reactivity of acyl chlorides in general can lead to a variety of products when paired with the right reactants.
  • Functional Group Transformation: The compound is also a precursor for introducing the phthaloyl group into other organic compounds, facilitating the formation of pharmaceuticals and other fine chemicals.
  • Environmental Considerations: Working with benzene-1,2-dicarbonyl chloride demands caution; like many acyl chlorides, it can release hydrochloric acid upon hydrolysis, necessitating proper safety measures in the laboratory.
  • Historical Context: The development of phthaloyl chloride and similar derivatives can be linked to the burgeoning field of synthetic organic chemistry, showcasing the innovative techniques employed by chemists to transform basic compounds into valuable products.

In summary, benzene-1,2-dicarbonyl chloride is not just a molecule of interest for its structure but also for its contributions to various fields of chemistry. As researchers continue to explore its reactivity, the potential applications of this compound are vast and varied, making it a staple in the toolkit of organic chemists.

Synonyms
Phthaloyl dichloride
PHTHALOYL CHLORIDE
88-95-9
o-Phthaloyl dichloride
Phthalic chloride
Phthalic dichloride
Phthalyl chloride
Phthalyl dichloride
Phthalic acid dichloride
1,2-Benzenedicarbonyl dichloride
benzene-1,2-dicarbonyl chloride
1,2-Bis(chlorocarbonyl)benzene
1,2-Phthaloyl dichloride
benzene-1,2-dicarbonyl dichloride
NSC 44611
EINECS 201-869-0
8S64APH24W
CCRIS 8625
NSC-44611
PHTHALOYL CHLORIDE [MI]
DTXSID8038691
O-PHTHALIC ACID DICHLORIDE
EC 201-869-0
Phthaloyldichloride
MFCD00000666
UNII-8S64APH24W
Pthaloyl chloride
phthalic dichoride
Phthaloyl chloride, 90%
SCHEMBL422
Phthaloyl chloride (8CI)
1,2Bis(chlorocarbonyl)benzene
1,2Benzenedicarbonyl dichloride
DTXCID6018691
NSC44611
STR02496
STL453643
TD1160
AKOS009029113
Phthaloyl chloride, technical, >=90%
DB-057111
NS00002449
P0405
EN300-19274
A15044
A843009
Q27270948
F1905-7003
201-869-0